Yıl 2024,
Cilt: 17 Sayı: 2, 474 - 487, 31.08.2024
Şule Gürsoy
,
Elif Şevval Öztürk
,
Bayan Zoatier
,
Mahmut Ülger
,
Öztekin Algül
Proje Numarası
TYL-2023-944
Kaynakça
- [1] Nyarko, R.O., Prakash, A., Kumar, N., Saha, P., and Kumar, R. (2021) Tuberculosis a globalized disease: Review. Asian Journal of Pharmaceutical Research and Development. 9 (1), 198–201.
- [2] Stubbs, B., Siddiqi, K., Elsey, H., Siddiqi, N., Ma, R., Romano, E., et al. (2021) Tuberculosis and Non-Communicable Disease Multimorbidity: An Analysis of the World Health Survey in 48 Low- and Middle-Income Countries. International Journal of Environmental Research and Public Health. 18 (5), 2439.
- [3] Sultana, Z.Z., Hoque, F.U., Beyene, J., Akhlak-Ul-Islam, Md., Khan, M.H.R., Ahmed, S., et al. (2021) HIV infection and multidrug resistant tuberculosis: a systematic review and meta-analysis. BMC Infectious Diseases. 21 (1), 51.
- [4] WHO (2023) Global Tuberculosis Report 2023. Https://Www.Who.Int/Teams/Global-Tuberculosis-Programme/Tb-Reports/Global-Tuberculosis-Report-2023.
- [5] Hernández-López, H., Tejada-Rodríguez, C.J., and Leyva-Ramos, S. (2022) A Panoramic Review of Benzimidazole Derivatives and their Potential Biological Activity. Mini-Reviews in Medicinal Chemistry. 22 (9), 1268–1280.
- [6] Yadav, K.P., Rahman, M.A., Nishad, S., Maurya, S.K., Anas, M., and Mujahid, M. (2023) Synthesis and biological activities of benzothiazole derivatives: A review. Intelligent Pharmacy. 1 (3), 122–132.
- [7] Sattar, R., Mukhtar, R., Atif, M., Hasnain, M., and Irfan, A. (2020) Synthetic transformations and biological screening of benzoxazole derivatives: A review. Journal of Heterocyclic Chemistry. 57 (5), 2079–2107.
- [8] Zoatier, B., Yildirim, M., Alagoz, M.A., Yetkin, D., Turkmenoglu, B., Burmaoglu, S., et al. (2023) N-(benzazol-2-yl)-2-substituted phenylacetamide derivatives: Design, synthesis and biological evaluation against MCF7 breast cancer cell line. Journal of Molecular Structure. 1285 135513.
- [9] Yalcin-Ozkat, G., Ersan, R.H., Ulger, M., Ulger, S.T., Burmaoglu, S., Yildiz, I., et al. (2023) Design, synthesis, and computational studies of benzimidazole derivatives as new antitubercular agents. Journal of Biomolecular Structure and Dynamics. 41 (7), 2667–2686.
- [10] Veena, K., Raghu, M.S., Yogesh Kumar, K., Pradeep Kumar, C.B., Alharti, F.A., Prashanth, M.K., et al. (2022) Design and synthesis of novel benzimidazole linked thiazole derivatives as promising inhibitors of drug-resistant tuberculosis. Journal of Molecular Structure. 1269 133822.
- [11] Panneerselvam, T., Kunjiappan, S., Alagarsamy, V., Saravanan, G., and Parasuraman, P. (2020) Design, Optimization, Synthesis and AntiTB Screening of Benzimidazole Derivatives. Anti-Infective Agents. 18 (1), 24–42.
- [12] Yadav, R., Meena, D., Singh, K., Tyagi, R., Yadav, Y., and Sagar, R. (2023) Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds. RSC Advances. 13 (32), 21890–21925.
- [13] Bhat, M. and Belagali, S.L. (2020) Structural Activity Relationship and Importance of Benzothiazole Derivatives in Medicinal Chemistry: A Comprehensive Review. Mini-Reviews in Organic Chemistry. 17 (3), 323–350.
- [14] Hemeda, L.R., El Hassab, M.A., Abdelgawad, M.A., Khaleel, E.F., Abdel-Aziz, M.M., Binjubair, F.A., et al. (2023) Discovery of pyrimidine-tethered benzothiazole derivatives as novel anti-tubercular agents towards multi- and extensively drug resistant Mycobacterium tuberculosis. Journal of Enzyme Inhibition and Medicinal Chemistry. 38 (1),.
- [15] Sumit, Kumar, A., and Mishra, A.K. (2021) Advancement in Pharmacological Activities of Benzothiazole and its Derivatives: An Up to Date Review. Mini-Reviews in Medicinal Chemistry. 21 (3), 314–335.
- [16] Kamal, U., Javed, N.M., And Arun, K. (2020) Bıologıcal Potentıal Of Benzoxazole Derıvatıves: An Updated Revıew. Asian Journal of Pharmaceutical and Clinical Research. 28–41.
- [17] Kumar, G., Chauhan, B., Singh, S., and Negi, M. (2022) In-Silico Prediction and Docking Studies Of Novel Synthesized Benzoxazole Derivatives As Anti-Tubercular Activity. Journal Of Pharmaceutical Negative Results. 13 (9), 9216–9226.
- [18] Sattar, R., Mukhtar, R., Atif, M., Hasnain, M., and Irfan, A. (2020) Synthetic transformations and biological screening of benzoxazole derivatives: A review. Journal of Heterocyclic Chemistry. 57 (5), 2079–2107.
- [19] Ayaz, F., Kheeree, R., Isse, Q.A., Ersan, R.H., and Algul, O. (2018) DNA Base Bioisosteres, Bis-benzoxazoles, Exert Anti-proliferative Effect on Human Prostate and Breast Cancer Cells. Journal of the Turkish Chemical Society Section A: Chemistry. 5 (3), 1145–1152.
- [20] Keri, R.S., Rajappa, C.K., Patil, S.A., and Nagaraja, B.M. (2016) Benzimidazole-core as an antimycobacterial agent. Pharmacological Reports. 68 (6), 1254–1265.
- [21] Akhtar, W., Khan, M.F., Verma, G., Shaquiquzzaman, M., Rizvi, M.A., Mehdi, S.H., et al. (2017) Therapeutic evolution of benzimidazole derivatives in the last quinquennial period. European Journal of Medicinal Chemistry. 126 705–753.
- [22] Bansal, Y. and Silakari, O. (2012) The therapeutic journey of benzimidazoles: A review. Bioorganic & Medicinal Chemistry. 20 (21), 6208–6236.
- [23] Park, B., Awasthi, D., Chowdhury, S.R., Melief, E.H., Kumar, K., Knudson, S.E., et al. (2014) Design, synthesis and evaluation of novel 2,5,6-trisubstituted benzimidazoles targeting FtsZ as antitubercular agents. Bioorganic & Medicinal Chemistry. 22 (9), 2602–2612.
- [24] Kalalbandi, V.K.A., Seetharamappa, J., Katrahalli, U., and Bhat, K.G. (2014) Synthesis, crystal studies, anti-tuberculosis and cytotoxic studies of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives. European Journal of Medicinal Chemistry. 79 194–202.
- [25] Gobis, K., Foks, H., Serocki, M., Augustynowicz-Kopeć, E., and Napiórkowska, A. (2015) Synthesis and evaluation of in vitro antimycobacterial activity of novel 1H-benzo[d]imidazole derivatives and analogues. European Journal of Medicinal Chemistry. 89 13–20.
- [26] Awasthi, D., Kumar, K., Knudson, S.E., Slayden, R.A., and Ojima, I. (2013) SAR Studies on Trisubstituted Benzimidazoles as Inhibitors of Mtb FtsZ for the Development of Novel Antitubercular Agents. Journal of Medicinal Chemistry. 56 (23), 9756–9770.
- [27] Antoci, V., Cucu, D., Zbancioc, G., Moldoveanu, C., Mangalagiu, V., Amariucai-Mantu, D., et al. (2020) Bis-(imidazole/benzimidazole)-pyridine derivatives: synthesis, structure and antimycobacterial activity. Future Medicinal Chemistry. 12 (3), 207–222.
- [28] Barcin, T., Yucel, M.A., Ersan, R.H., Alagoz, M.A., Dogen, A., Burmaoglu, S., et al. (2024) Deep learning approach to the discovery of novel bisbenzazole derivatives for antimicrobial effect. Journal of Molecular Structure. 1295 136668.
- [29] Ersan, R.H., Alagoz, M.A., Dogen, A., Duran, N., Burmaoglu, S., and Algul, O. (2022) Bisbenzoxazole Derivatives: Design, Synthesis, in Vitro Antimicrobial, Antiproliferative Activity, and Molecular Docking Studies. Polycyclic Aromatic Compounds. 42 (6), 3103–3123.
- [30] Ersan, R.H., Bolelli, K., Gonca, S., Dogen, A., Burmaoglu, S., and Algul, O. (2021) Bisbenzimidazole Derivatives as Potential Antimicrobial Agents: Design, Synthesis, Biological Evaluation and Pharmacophore Analysis. Pharmaceutical Chemistry Journal. 55 (2), 149–158.
- [31] Wieland, T. and Bodanszky, M. (1991) The World of Peptides. Springer Berlin Heidelberg, Berlin, Heidelberg.
- [32] Scattolin, T., Bouayad-Gervais, S., and Schoenebeck, F. (2019) Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas. Nature. 573 (7772), 102–107.
- [33] de Figueiredo, R.M., Suppo, J.-S., and Campagne, J.-M. (2016) Nonclassical Routes for Amide Bond Formation. Chemical Reviews. 116 (19), 12029–12122.
- [34] Pattabiraman, V.R. and Bode, J.W. (2011) Rethinking amide bond synthesis. Nature. 480 (7378), 471–479.
- [35] Veena, K., Raghu, M.S., Yogesh Kumar, K., Pradeep Kumar, C.B., Alharti, F.A., Prashanth, M.K., et al. (2022) Design and synthesis of novel benzimidazole linked thiazole derivatives as promising inhibitors of drug-resistant tuberculosis. Journal of Molecular Structure. 1269 133822.
- [36] Šlachtová, V., & Brulíková, L. (2018). Benzoxazole derivatives as promising antitubercular agents. ChemistrySelect, 3(17), 4653-4662.
- [37] Yadav, R., Meena, D., Singh, K., Tyagi, R., Yadav, Y., & Sagar, R. (2023). Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds. RSC Advances, 13(32), 21890-21925.
- [38] Fu, Y., O’Connor, L.M., Shepherd, T.G., and Nachtigal, M.W. (2003) The p38 MAPK inhibitor, PD169316, inhibits transforming growth factor β-induced Smad signaling in human ovarian cancer cells. Biochemical and Biophysical Research Communications. 310 (2), 391–397.
- [39] Susceptibility Testing of Mycobacteria, Nocardiae, and Other Aerobic Actinomycetes. 2nd ed. Wayne, Pennsylvania. (2011)
- [40] Denizot, F. and Lang, R. (1986) Rapid colorimetric assay for cell growth and survival. Journal of Immunological Methods. 89 (2), 271–277.
- [41] Mosmann, T. (1983) Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods. 65 (1–2), 55–63.
- [42] Schrödinger (2024) Schrödinger Release 2024-1: QikProp.
- [43] Burmaoglu, S., Algul, O., Gobek, A., Aktas Anil, D., Ulger, M., Erturk, B.G., et al. (2017) Design of potent fluoro-substituted chalcones as antimicrobial agents. Journal of Enzyme Inhibition and Medicinal Chemistry. 32 (1), 490–495.
- [44] S. Maia, M., de Sousa, N.F., Rodrigues, G.C.S., Monteiro, A.F.M., Scotti, M.T., and Scotti, L. (2020) Lignans and Neolignans Anti-tuberculosis Identified by QSAR and Molecular Modeling. Combinatorial Chemistry & High Throughput Screening. 23 (6), 504–516.
Synthesis and antitubercular activities of acetamide-substituted benzazole derivatives
Yıl 2024,
Cilt: 17 Sayı: 2, 474 - 487, 31.08.2024
Şule Gürsoy
,
Elif Şevval Öztürk
,
Bayan Zoatier
,
Mahmut Ülger
,
Öztekin Algül
Öz
Multidrug-resistant Mycobacterium tuberculosis strains' increasing emergence and rapid spread necessitate the urgent development of innovative antimycobacterial agents. In pursuit of novel agents, a series of N-(benzazole-2-ylmethyl)-2-substituted phenylacetamide or N-(benzazole-2-ylmethyl)-2-(thiophen-2-yl)acetamide compounds (6-11) were synthesized. Their efficacy against multidrug-resistant Mycobacterium tuberculosis was assessed. Compounds exhibited potent antimycobacterial activity with minimum inhibitory concentrations (MIC) ranging from 1.05 to 4.10 µM and demonstrated low cytotoxicity towards fibroblast cell line (L929). ADMET predictions suggested that these synthesized compounds possess drug-like properties. Our findings offer a promising starting point for designing more selective and potent antimycobacterial agents.
Etik Beyan
Gerekli değildir
Destekleyen Kurum
Research Fund of Erzincan Binali Yıldırım University
Proje Numarası
TYL-2023-944
Teşekkür
This study is funded by the Research Fund of Erzincan Binali Yıldırım University, Turkey (Project number: TYL-2023-944). We would like to thank Erzincan Binali Yıldırım University for its support.
Kaynakça
- [1] Nyarko, R.O., Prakash, A., Kumar, N., Saha, P., and Kumar, R. (2021) Tuberculosis a globalized disease: Review. Asian Journal of Pharmaceutical Research and Development. 9 (1), 198–201.
- [2] Stubbs, B., Siddiqi, K., Elsey, H., Siddiqi, N., Ma, R., Romano, E., et al. (2021) Tuberculosis and Non-Communicable Disease Multimorbidity: An Analysis of the World Health Survey in 48 Low- and Middle-Income Countries. International Journal of Environmental Research and Public Health. 18 (5), 2439.
- [3] Sultana, Z.Z., Hoque, F.U., Beyene, J., Akhlak-Ul-Islam, Md., Khan, M.H.R., Ahmed, S., et al. (2021) HIV infection and multidrug resistant tuberculosis: a systematic review and meta-analysis. BMC Infectious Diseases. 21 (1), 51.
- [4] WHO (2023) Global Tuberculosis Report 2023. Https://Www.Who.Int/Teams/Global-Tuberculosis-Programme/Tb-Reports/Global-Tuberculosis-Report-2023.
- [5] Hernández-López, H., Tejada-Rodríguez, C.J., and Leyva-Ramos, S. (2022) A Panoramic Review of Benzimidazole Derivatives and their Potential Biological Activity. Mini-Reviews in Medicinal Chemistry. 22 (9), 1268–1280.
- [6] Yadav, K.P., Rahman, M.A., Nishad, S., Maurya, S.K., Anas, M., and Mujahid, M. (2023) Synthesis and biological activities of benzothiazole derivatives: A review. Intelligent Pharmacy. 1 (3), 122–132.
- [7] Sattar, R., Mukhtar, R., Atif, M., Hasnain, M., and Irfan, A. (2020) Synthetic transformations and biological screening of benzoxazole derivatives: A review. Journal of Heterocyclic Chemistry. 57 (5), 2079–2107.
- [8] Zoatier, B., Yildirim, M., Alagoz, M.A., Yetkin, D., Turkmenoglu, B., Burmaoglu, S., et al. (2023) N-(benzazol-2-yl)-2-substituted phenylacetamide derivatives: Design, synthesis and biological evaluation against MCF7 breast cancer cell line. Journal of Molecular Structure. 1285 135513.
- [9] Yalcin-Ozkat, G., Ersan, R.H., Ulger, M., Ulger, S.T., Burmaoglu, S., Yildiz, I., et al. (2023) Design, synthesis, and computational studies of benzimidazole derivatives as new antitubercular agents. Journal of Biomolecular Structure and Dynamics. 41 (7), 2667–2686.
- [10] Veena, K., Raghu, M.S., Yogesh Kumar, K., Pradeep Kumar, C.B., Alharti, F.A., Prashanth, M.K., et al. (2022) Design and synthesis of novel benzimidazole linked thiazole derivatives as promising inhibitors of drug-resistant tuberculosis. Journal of Molecular Structure. 1269 133822.
- [11] Panneerselvam, T., Kunjiappan, S., Alagarsamy, V., Saravanan, G., and Parasuraman, P. (2020) Design, Optimization, Synthesis and AntiTB Screening of Benzimidazole Derivatives. Anti-Infective Agents. 18 (1), 24–42.
- [12] Yadav, R., Meena, D., Singh, K., Tyagi, R., Yadav, Y., and Sagar, R. (2023) Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds. RSC Advances. 13 (32), 21890–21925.
- [13] Bhat, M. and Belagali, S.L. (2020) Structural Activity Relationship and Importance of Benzothiazole Derivatives in Medicinal Chemistry: A Comprehensive Review. Mini-Reviews in Organic Chemistry. 17 (3), 323–350.
- [14] Hemeda, L.R., El Hassab, M.A., Abdelgawad, M.A., Khaleel, E.F., Abdel-Aziz, M.M., Binjubair, F.A., et al. (2023) Discovery of pyrimidine-tethered benzothiazole derivatives as novel anti-tubercular agents towards multi- and extensively drug resistant Mycobacterium tuberculosis. Journal of Enzyme Inhibition and Medicinal Chemistry. 38 (1),.
- [15] Sumit, Kumar, A., and Mishra, A.K. (2021) Advancement in Pharmacological Activities of Benzothiazole and its Derivatives: An Up to Date Review. Mini-Reviews in Medicinal Chemistry. 21 (3), 314–335.
- [16] Kamal, U., Javed, N.M., And Arun, K. (2020) Bıologıcal Potentıal Of Benzoxazole Derıvatıves: An Updated Revıew. Asian Journal of Pharmaceutical and Clinical Research. 28–41.
- [17] Kumar, G., Chauhan, B., Singh, S., and Negi, M. (2022) In-Silico Prediction and Docking Studies Of Novel Synthesized Benzoxazole Derivatives As Anti-Tubercular Activity. Journal Of Pharmaceutical Negative Results. 13 (9), 9216–9226.
- [18] Sattar, R., Mukhtar, R., Atif, M., Hasnain, M., and Irfan, A. (2020) Synthetic transformations and biological screening of benzoxazole derivatives: A review. Journal of Heterocyclic Chemistry. 57 (5), 2079–2107.
- [19] Ayaz, F., Kheeree, R., Isse, Q.A., Ersan, R.H., and Algul, O. (2018) DNA Base Bioisosteres, Bis-benzoxazoles, Exert Anti-proliferative Effect on Human Prostate and Breast Cancer Cells. Journal of the Turkish Chemical Society Section A: Chemistry. 5 (3), 1145–1152.
- [20] Keri, R.S., Rajappa, C.K., Patil, S.A., and Nagaraja, B.M. (2016) Benzimidazole-core as an antimycobacterial agent. Pharmacological Reports. 68 (6), 1254–1265.
- [21] Akhtar, W., Khan, M.F., Verma, G., Shaquiquzzaman, M., Rizvi, M.A., Mehdi, S.H., et al. (2017) Therapeutic evolution of benzimidazole derivatives in the last quinquennial period. European Journal of Medicinal Chemistry. 126 705–753.
- [22] Bansal, Y. and Silakari, O. (2012) The therapeutic journey of benzimidazoles: A review. Bioorganic & Medicinal Chemistry. 20 (21), 6208–6236.
- [23] Park, B., Awasthi, D., Chowdhury, S.R., Melief, E.H., Kumar, K., Knudson, S.E., et al. (2014) Design, synthesis and evaluation of novel 2,5,6-trisubstituted benzimidazoles targeting FtsZ as antitubercular agents. Bioorganic & Medicinal Chemistry. 22 (9), 2602–2612.
- [24] Kalalbandi, V.K.A., Seetharamappa, J., Katrahalli, U., and Bhat, K.G. (2014) Synthesis, crystal studies, anti-tuberculosis and cytotoxic studies of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives. European Journal of Medicinal Chemistry. 79 194–202.
- [25] Gobis, K., Foks, H., Serocki, M., Augustynowicz-Kopeć, E., and Napiórkowska, A. (2015) Synthesis and evaluation of in vitro antimycobacterial activity of novel 1H-benzo[d]imidazole derivatives and analogues. European Journal of Medicinal Chemistry. 89 13–20.
- [26] Awasthi, D., Kumar, K., Knudson, S.E., Slayden, R.A., and Ojima, I. (2013) SAR Studies on Trisubstituted Benzimidazoles as Inhibitors of Mtb FtsZ for the Development of Novel Antitubercular Agents. Journal of Medicinal Chemistry. 56 (23), 9756–9770.
- [27] Antoci, V., Cucu, D., Zbancioc, G., Moldoveanu, C., Mangalagiu, V., Amariucai-Mantu, D., et al. (2020) Bis-(imidazole/benzimidazole)-pyridine derivatives: synthesis, structure and antimycobacterial activity. Future Medicinal Chemistry. 12 (3), 207–222.
- [28] Barcin, T., Yucel, M.A., Ersan, R.H., Alagoz, M.A., Dogen, A., Burmaoglu, S., et al. (2024) Deep learning approach to the discovery of novel bisbenzazole derivatives for antimicrobial effect. Journal of Molecular Structure. 1295 136668.
- [29] Ersan, R.H., Alagoz, M.A., Dogen, A., Duran, N., Burmaoglu, S., and Algul, O. (2022) Bisbenzoxazole Derivatives: Design, Synthesis, in Vitro Antimicrobial, Antiproliferative Activity, and Molecular Docking Studies. Polycyclic Aromatic Compounds. 42 (6), 3103–3123.
- [30] Ersan, R.H., Bolelli, K., Gonca, S., Dogen, A., Burmaoglu, S., and Algul, O. (2021) Bisbenzimidazole Derivatives as Potential Antimicrobial Agents: Design, Synthesis, Biological Evaluation and Pharmacophore Analysis. Pharmaceutical Chemistry Journal. 55 (2), 149–158.
- [31] Wieland, T. and Bodanszky, M. (1991) The World of Peptides. Springer Berlin Heidelberg, Berlin, Heidelberg.
- [32] Scattolin, T., Bouayad-Gervais, S., and Schoenebeck, F. (2019) Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas. Nature. 573 (7772), 102–107.
- [33] de Figueiredo, R.M., Suppo, J.-S., and Campagne, J.-M. (2016) Nonclassical Routes for Amide Bond Formation. Chemical Reviews. 116 (19), 12029–12122.
- [34] Pattabiraman, V.R. and Bode, J.W. (2011) Rethinking amide bond synthesis. Nature. 480 (7378), 471–479.
- [35] Veena, K., Raghu, M.S., Yogesh Kumar, K., Pradeep Kumar, C.B., Alharti, F.A., Prashanth, M.K., et al. (2022) Design and synthesis of novel benzimidazole linked thiazole derivatives as promising inhibitors of drug-resistant tuberculosis. Journal of Molecular Structure. 1269 133822.
- [36] Šlachtová, V., & Brulíková, L. (2018). Benzoxazole derivatives as promising antitubercular agents. ChemistrySelect, 3(17), 4653-4662.
- [37] Yadav, R., Meena, D., Singh, K., Tyagi, R., Yadav, Y., & Sagar, R. (2023). Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds. RSC Advances, 13(32), 21890-21925.
- [38] Fu, Y., O’Connor, L.M., Shepherd, T.G., and Nachtigal, M.W. (2003) The p38 MAPK inhibitor, PD169316, inhibits transforming growth factor β-induced Smad signaling in human ovarian cancer cells. Biochemical and Biophysical Research Communications. 310 (2), 391–397.
- [39] Susceptibility Testing of Mycobacteria, Nocardiae, and Other Aerobic Actinomycetes. 2nd ed. Wayne, Pennsylvania. (2011)
- [40] Denizot, F. and Lang, R. (1986) Rapid colorimetric assay for cell growth and survival. Journal of Immunological Methods. 89 (2), 271–277.
- [41] Mosmann, T. (1983) Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods. 65 (1–2), 55–63.
- [42] Schrödinger (2024) Schrödinger Release 2024-1: QikProp.
- [43] Burmaoglu, S., Algul, O., Gobek, A., Aktas Anil, D., Ulger, M., Erturk, B.G., et al. (2017) Design of potent fluoro-substituted chalcones as antimicrobial agents. Journal of Enzyme Inhibition and Medicinal Chemistry. 32 (1), 490–495.
- [44] S. Maia, M., de Sousa, N.F., Rodrigues, G.C.S., Monteiro, A.F.M., Scotti, M.T., and Scotti, L. (2020) Lignans and Neolignans Anti-tuberculosis Identified by QSAR and Molecular Modeling. Combinatorial Chemistry & High Throughput Screening. 23 (6), 504–516.